Vacation Rentals By Owner In Orangeville, ON

Welcome to our newly renovated 700 sq ft basement apartment with full kitchen. brbrCentrally located we're a 2 min walk to the hospital, a 5 min drive to Orangeville's two hockey arenas and a short drive to downtown.brbrFree parking for one car on the driveway, unlimited free parking on the street 24/7 from May to October.

Cozy Basement Apartment (700 sq ft) with Full Kitchen

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(4)

$256.4

Perfect getaway for you to relax and stroll through the gardens, catch minnows and explore the wonders of the Nottawasaga as you enjoy this beautiful peaceful environment. This lower level walk out apartment features a comfy queen bed, living room area and small kitchenette with sink, microwave, hotplate and fridge/freezer. Ideal for a solo traveler or couple. There is a BBQ outdoor to grill and plenty of areas to sit and enjoy the surrounding tranquility.

Condo

Hockley Valley Riverfront Condo #2 - Minutes To Hockley Ski Resort & Winery

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(1)

$412.59

Summary:brbrWelcome to my spacious riverfront retreat, perfect for up to 10 guests! This 5-bedroom, 3-bathroom home features 4 queen beds, 1 king bed, and a bathtub. Enjoy outdoor dining on the beautiful deck with a firetable, BBQ grill, and over 1000 ft of river frontage on 72 acres. Inside, you'll find a Smart TV, thermostat, washer/dryer, and ample parking with 6+ spots. Garbage bins are located in the garage for your convenience. Relax and unwind in this serene and well-equipped getawaybrbrbrbrThe Space:brbr✪ Property Detailsbrbr➜Approx. 3800 ft² / 353 m² of space.brbr➜1 000+ FT of river frontage, 72 acres!brbrbrbr✪ Outdoor Featuresbrbr➜Firetable/dining table set on the beautiful deck.brbr➜BBQ grill for outdoor cooking and dining.brbr➜ Relax by the firepit. brbrbrbr✪Technology and Entertainmentbrbr➜Highspeed internet access.brbr➜Smart TV from which you can enjoy access to your Netflix or YouTube.brbrbrbr✪ Sleeping Arrangementsbrbr➜Master bedroom features King size bed.brbr➜Bedroom 2 features Queen size bed.brbr➜Bedroom 3 features a Queen size bed.brbr➜Bedroom 4 features a Queen size bed.brbr➜Bedroom 5 features a Queen size bed.brbrbrbr✪ Bathroomsbrbr➜3 clean and sanitized full bathrooms with essentials.brbrbrbr✪ Laundrybrbr➜In-house washer and dryer machines.brbrbrbr✪ Linens and Towelsbrbr➜Full sets of hotel-quality sheets and duvets for the beds and enough towels.brbrbrbr✪ Kitchenbrbr➜Kitchen is fully equipped with appliances including a large fridge and stove.brbrbrbr➤ IMPORTANT NOTE FOR 1 WEEK STAY OR LONGER:brbrToilet paper, garbage bags, and basic toiletries will be provided for the guests at the beginning of the stay. It will then be the guest's responsibility to provide for these for the remainder of their stay.brbrbrbrGuest Access:brbr➤ Guests will have access to the entire unit. Please, make yourself at home.brbrbrbrbrbr➤ Availability of 6+ driveway parking spotsbrbrbrbrThe Neighborhood:brbrNestled in a picturesque rural area, this location offers a perfect blend of tranquility and natural beauty. Surrounded by lush greenery and rolling hills, it's an ideal retreat for those looking to escape the hustle and bustle of city life. brbrbrbrThe nearby river provides ample opportunities for fishing, kayaking, and leisurely strolls along its banks. Local attractions include charming farms, quaint shops, and cozy cafes, making it a delightful spot to explore and unwind. brbrbrbrThe community is known for its friendly residents and a relaxed atmosphere, ensuring a warm and welcoming experience.brbrbrbrGetting Around:brbrCar Required: A car is essential for getting around due to the rural setting and limited public transportation options.brbrbrbrNearby Towns: The closest towns, with grocery stores, restaurants, and other amenities, are a short drive away.brbrbrbrOutdoor Activities: The area is ideal for outdoor enthusiasts, with nearby hiking trails, river activities, and scenic drives.brbrbrbrNavigation: GPS and maps are recommended for navigation, as rural roads can be less straightforward and signage limited.brbrbrbrOther Things to Note:brbr➤ My place does come with heating and A/C, but I can't promise you'll hit that comfy spot if your ideal temp is below 17 or above 25 degrees Celsius. And, you know how it is with short-term rentals – folks are always coming and going. So, I can't guarantee a flawless run all the time because, truth be told, some guests tend to go overboard and push the systems to the point where repairs are needed.brbrbrbr➤ Unfortunately, I can't offer a bag drop-off service. For those arriving early or having a late flight, you can use bagbnb site to find options to drop off your bag for a fee.brbrbrbrInteraction with Guests:brbrI will be your personal concierge for your stay. If you have any questions, you’re lost, or just need some great recommendations, I’ll be there for you around the clock.

5BR Riverfront Retreat w/ Firetable, BBQ, and Deck

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(14)

$71.15

Come & unwind...in comfort.brbrThe Snug is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Amazing kitchen, sleek 3 pc bathroom with rainfall shower head. The queen bed with luxury-firm mattress, has built in storage for all your needs. Dinner table expands for meals, games or working at home!brbrA short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

A bright & modern urban studio

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(30)

$74.3

Entire ground level walkout basement with lots of exposure to natural light. It's fully equipped with 1 private bedroom & 1 additional bed in living area with a scenic view of backyard .Attached Private Washroom to bedroom is available . High speed internet is available.Parking spot on the property. Small bar fridge & microwave available in basement .

Entire place, Ground level walkout Basement with Huge backyard

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(18)

$164.43

Experience the sights and sounds of nature during your stay- with surrounding greenery and a bustling brook just outside. The cottage has a very inviting and comfy living room setting, a cozy upstairs space, a welcoming kitchenette and a stylish bathroom/shower.

Cottage

Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$285.56

Book this listing directly at www.kozinestrentals.com and save up to 20%brbrWelcome to our spacious and fully furnished 4-bedroom, 2.5-bathroom single-family home in the heart of Orangeville! Just a 10-minute walk to Headwaters Health Care Centre and a 5-minute drive to Mount Alverno Luxury Resorts. Enjoy fast, free Wi‑Fi and a Smart TV with streaming. Explore Island Lake Conservation Area, scenic trails, local parks, and charming Broadway boutiques and cafés. Perfect for medical stays, business trips, outdoor escapes, or memorable times with family and friends!brbrInside, you’ll find a bright and inviting living area with plenty of seating and a large flat-screen TV—perfect for relaxing after a busy day. The fully equipped kitchen includes a refrigerator, stove, oven, microwave, and essential cookware, along with ample counter space and cabinetry for meal prep. The adjacent dining area seats six comfortably, making it easy to gather for meals or plan your day together.brbrThe home features three queen beds and one king bed in the master bedroom. The master bedroom also boasts an en-suite bathroom with a separate bathtub and shower. A second full bathroom with a separate bathtub and shower is conveniently located for other guests, while a half bathroom on the main level adds extra convenience.brbrStep outside to enjoy the deck—perfect for relaxing with a patio set that includes a table, umbrella, and 4 folding chairs. The ground-level laundry room with a washer and dryer makes longer stays even easier.brbrAdditional amenities include complimentary Wi-Fi, heating, and air conditioning.brbrThis well-equipped home offers a clean, private, and comfortable base for your stay in Orangeville.

Spacious Cozy 4BR Orangeville Home w/Deck! 10-minute walk to Headwaters Hospital

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(8)

$159.2

Come & relax...in privacy.brbrThe Cooper is an 833 square foot 2 bedroom that is unique & intimate. You will be on the main floor of the main house, with a basement apartment below you. Amazing kitchen, complete with gas range & dishwasher. Primary bedroom has in suite laundry, & the elegant bathroom has heated floors! Exclusive entrance and private outdoor area with BBQ.brbrA short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

A bright & chic 2 bedroom urban apartment

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(3)

$109.38

Please mention guest correctly for booking request. Listed price is for Single guest. If more than 1 guest, please select accordingly to see the correct price. brbrPlease confirm car type for parking availability. Have parking for Regular size car. I have Tesla charger at home, if you gonna charge during. your stay please confirm, charging is extra $$.brbrIndian Breakfast provided with extra cost.brbrBest for couples, or professionals looking for space to have great time away from home. Note : We apologize in advance, We are unable to host any pets, as myself and my Son have severe allergies. Any kind of Smoking is not allowed on premises.

Cozy One bedroom suite 5min to Orangeville Downtown

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(13)

$214.73

Discover an Elevated Outdoor RetreatbrExperience an outdoor escape in the heart of Mono, Ontario, where comfort meets nature. Located beside the scenic Avalon Lavender Farm and within a short drive to Mono Cliffs Provincial Park, Island Lake, and Hockley Valley, our glamping site offers a balance of seclusion and comfort.brbrEach site is a short walk from the main road, providing a peaceful natural setting. Privacy levels and views vary by site and season.brbrSpring, Summer & Fall GlampingbrbrFrom the vibrant greens of spring to the golden tones of autumn, Mono Pines Glamping offers a seasonal outdoor experience.brbrFeatures may include:brbrKing Bed Comfort – Plush bedding, side tables, and a loveseat for relaxing.brOutdoor Cooking & Dining– BBQ and private dining area *(operation subject to seasonal conditions, maintenance, and host discretion)*.brKitchenware Essentials – Basic utensils and drinkware.brEvening Ambiance – String lighting, an Iron Embers fire pit, and Muskoka chairs.brConvenient Extras – Handwashing station at the outhouse, outdoor dishwashing area, and a wagon for gear transport *(availability may vary)*.br*Seasonal Décor – Décor is refreshed periodically and varies by season.brbrWinter GlampingbrWinter stays typically include:brbrWood Stove Heating – Firewood and kindling provided. Guests are solely responsible for maintaining the fire to keep the tent warm; no other heat sources are provided.brComfort Additions – Plush bedding, a faux fur throw, and extra linens.brHot Beverage Station – Nespresso machine with condiments *(availability subject to availability maintenance)*.brIndoor Comfort – Loveseat, dimmable lighting, and winter décor.brPrivate Outhouse– Vented outhouse with Sunmar composting toilet.brOutdoor Space – Fire pit with Muskoka chairs *(use subject to weather conditions)*.brbrImportant NotesbrA reminder: this is still a camping experience and, although elevated with thoughtful comforts, it is not a full vacation rental or hotel.br*There is NO plumbed water on site.br* Amenities, features, and décor may vary by season, weather, and maintenance needs. Some items may be substituted, removed, or unavailable with reasonable notice for safety or operational reasons.br* The BBQ, dishwashing station, and water station are seasonal and may be unavailable during freezing temperatures or poor weather.br* Winter glamping is recommended for guests experienced in wood stove use and cold-weather camping.br* For the most current amenity list for your stay, please confirm with the host prior to arrival.brbrCheck-In OptionsbrEarly check-in is subject to host approval, availability, and an additional fee:brbr 12:00 pm – $75br 1:00 pm – $50br 2:00 pm – $25br Standard check-in is from 3:00 pm onward.brbrPet Policybrbr* Up to 2 pets permitted at $50 per night.br* All pets must be approved in advance.br* Unauthorized pets or unpaid pet fees will result in immediate cancellation of the booking, and guests will be required to vacate the property without refund.brbrCatering is available for an additional fee, contact your host for more details. *Subject to availability.

Caravan Park/Campsite

Glamping by Lavender Farm, Brewery, Mono Cliffs, Hockley Valley

Orangeville, Ontario, Canada

Bed

Sleeps

Exceptional(7)

$76.23

this peaceful and centrally located place in Orangeville downtown. Walking distance to lake conservation area, gym ,cineplex, retail plaza & broadway street. It’s an entire 600sqft bungalow, with 1 king size bed, 1 double bed in 2nd bedroom, living room has couch and TV, kitchen ,washroom , & backyard. 40 inch smart tv ,& wifi available.1 free parking.

Entire bungalow with 2 bedrooms,kitchen,washroom & privacy

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(5)

$268.21

Enjoy a stylish experience at this home centrally located Downtown Orangeville close to all amenities. Around beautiful hiking trails to explore!brbrComplementaries included with your stay:br- Heated blanket br- Prime Videobr- Water and Refreshments br- Coffee and Teabr- Fire place br- 3 Parking spaces

The Perfect Getaway

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(12)

$177.82

Centrally Located and walking distance to Downtown Orangeville or Island Lake Conservation areabrThis beautiful 2 bedroom, 1,250 sq ft unit sleeps 4 adults comfortably. brBedroom 1 has a queen-sized bed and a walk-out to the 2nd floor furnished patio area, while Bedroom 2 contains a full sized (double) bed. The highlights of this unit include the 2nd floor deck and a beautiful bathroom that has a separate shower and stand-alone “claw” bathtub.

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(20)

$195.14

Near Hockley Valley Resort and Osprey Golf etc . A 3-bedroom home with a new Gas Fireplace and 2 large HD Smart TVsbrThis 3 bedroom (4 beds), 1,500 sq ft unit sleeps 6 adults comfortably. Bedroom 1 and 2 have queen-sized beds, while Bedroom 2 contains two separate single beds. There is a large rear fenced yard and a deck/porch that contains a full-sized BBQ and ample outdoor space .Less than 5 Min walk to main Street ( Broadway)brPets allowed for a small additional feebrParking for up to 4 vehicles

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$208.17

Welcome to your serene countryside getaway in Mono, just minutes away from the vibrant charm of Orangeville. Nestled in the picturesque property backing directly on the tranquil Nottawasaga River, this cottage offers the perfect blend of natural beauty, privacy and plenty of adventures year-round. Wake up to the soothing sounds of the flowing river and enjoy your morning coffee by the warm fire. Whether you’re relaxing on the deck, exploring the riverbank, stargazing around the fire, this property is designed for slowing down and reconnecting with nature. Located in the stunning Hockley Valley, you can hike the breathtaking trails of Mono Cliffs Provincial Park, or visit local wineries cideries and farmer’s markets. Enjoy skiing and snowboarding in the winter, and hiking and cycling in the warmer months. Discover the shops, restaurants, and arts scene in downtown Orangeville. Visit the iconic “Rosebud Motel” from the hit TV show Schitt’s Creek, located less than 10 minutes away from the property. Just over an hour from Toronto, this hidden gem offers the ideal balance of accessibility and escape. Whether you’re here for adventure or relaxation, your riverside stay in Mono will be unforgettable!

Hockley Valley Cozy Cottage with Waterfront Access!

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Exceptional(5)

$148.33

Welcome to your perfect modern, stylish, and cozy get away. This home offers the spacious interiors, thoughtfully curated décor, and all the comforts of home. Located in the heart of town, you’ll have easy access to local ski attractions, dining, and entertainment, making it an ideal spot for both leisure and business travelers. Whether you’re unwinding in the beautifully designed living spaces or exploring the vibrant surroundings, this home is your perfect retreat.

Modern Cozy Getaway

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$118.39

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm apartment located downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Beautifully landscaped backyard with vegetable garden. Enjoy evening walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.brThe spacebrOne bedroom walkout garden apartment located in our home. The apartment features brand new kitchen, bathroom, wall mounted electric fireplace, wifi, gas bbq, patio, vegetable garden, fire pit.brGuest accessbrPrivate entrance. Full access to entire apartment. Partial access to backyard. Own private patio.brOther things to notebr***booking acceptance includes the agreement to waive any and all liability from the host from any and all use of this unit and the property.

Garden Studio Apartment

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

Most popular vacation rentals in Orangeville

$214.73

Caravan Park/Campsite

Glamping by Lavender Farm, Brewery, Mono Cliffs, Hockley Valley

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$195.14

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$177.82

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$109.38

Cozy One bedroom suite 5min to Orangeville Downtown

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$71.15

A bright & modern urban studio

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$159.20

A bright & chic 2 bedroom urban apartment

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$88.44

Guest house

A private & stylish urban studio

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$256.40

Condo

Hockley Valley Riverfront Condo #2 - Minutes To Hockley Ski Resort & Winery

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$148.33

Modern Cozy Getaway

Orangeville, Ontario, Canada

Bed

Bath

Sleeps

$164.43